title: C5 and C7 intramolecular hydrogen bonds stabilize the structure of N-pyrazinoyl-gabapentin (Pyr-Gpn-OH).
abstract: 2-{1-[(Pyrazin-2-ylformamido)methyl]cyclohexyl}acetic acid (Pyr-Gpn-OH), C14H19N3O3, is an N-protected derivative of gabapentin (Gpn). The compound crystallizes in the triclinic space group P1 and the molecular conformation is stabilized by intramolecular five- (C5) and seven-membered (C7) hydrogen-bonded rings. The packing of the molecules reveals intermolecular O-H···O and C-H···N hydrogen bonds, together with π-π interactions.
authors.affiliation: Medicinal Chemistry Division, Indian Institute of Integrative Medicine, Canal Road, Jammu Tawi 180 001, India.
authors.forename: Naiem Ahmad
authors.initials: NA
authors.lastname: Wani
authors.forename: Vivek Kumar
authors.initials: VK
authors.lastname: Gupta
authors.forename: Rajni
authors.initials: R
authors.lastname: Kant
authors.forename: Subrayashastry
authors.initials: S
authors.lastname: Aravinda
authors.forename: Rajkishor
authors.initials: R
authors.lastname: Rai
mesh_terms: D000588:Amines / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003509:Cyclohexanecarboxylic Acids / Q000737:chemistry*; D003510:Cyclohexanes / Q000737:chemistry*; D000077206:Gabapentin; D006860:Hydrogen Bonding; D008968:Molecular Conformation; D015394:Molecular Structure; D011719:Pyrazines / Q000737:chemistry*; D005680:gamma-Aminobutyric Acid / Q000737:chemistry*
chemical_list: C587108:2-(1-((pyrazin-2-ylformamido)methyl)cyclohexyl)acetic acid; D000588:Amines; D003509:Cyclohexanecarboxylic Acids; D003510:Cyclohexanes; D011719:Pyrazines; D005680:gamma-Aminobutyric Acid; D000077206:Gabapentin
keywords: conformation; crystal structure; gabapentin; hydrogen bonding; π–π interactions